1. Field of the Invention
The present invention relates to a quinoline compound suited for use in a luminous layer of an electro-luminescence element, the electro-luminescence element and a fluorescent material by using said compound, and a preparation process of said compound.
The invention also relates to a zinc halogenide complex suited for use in a luminous layer of an electro-luminescence element or an ultraviolet absorption material, the electro-luminescence element and the ultraviolet absorption material by using said complex, and a preparation process of said complex.
The invention further relates to a zinc complex suited for use in a luminous layer of an electro-luminescence element or an ultraviolet absorption material, the electro-luminescence element and the ultraviolet absorption material by using said complex, and a preparation process of said complex.
2. Related Art of the Invention
In recent years, a great deal of research a great deal of research on fluorescent materials and luminescent materials have been carried out in order to use these materials for electro-luminescence (EL) elements.
A quinoline having the formula (7): 
has been known to have fluorescent property as described in Liebigs Ann. Chem., vol.315, p.303(1901) and Chem. Ber., vol.100, p. 2261-2273 (1967).
On the other hand, the EL elements have recently attained a great progress. Luminous layers and positive hole transport layers have been investigated and are approaching practical use [Tsutsui, Saito et. al., Japan Journal of Applied Physics, vol.27, No.2, L269 (1988); vol.27, No.4,L713(1988)].
Aromatic compounds which exhibit fluorescence in the ultraviolet to visible region have been known [I. B. Berlman, Handbook of Fluorescence Spectra of Aromatic Molecules, published from Academic Press].
Further, inorganic compounds such as titanium dioxide and zinc oxide, and organic compounds such as benzophenone, benzotriazole and other compounds having a triazine structure have been known as ultraviolet absorption materials as disclosed in Japanese Laid-Open Patent Sho 64-20248.
The first object of the invention is to provide an excellent material as an EL material and a useful preparation process of the material.
The second object of the invention is to provide an excellent material as a fluorescent material and a useful preparation process of the material.
Further, the third object of the invention is to provide an excellent material as an ultraviolet absorption material and a useful preparation process of the material.
These objects can be achieved by the following aspects of the present invention.
(1) A quinoline compound and a tautomer of the same which are represented by the formula (1): 
where each of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 is individually a hydrogen atom, halogen atom, cyano, amino, substituted or unsubstituted alkyl having two or more carbon atoms substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, except the case where all of R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 is a hydrogen atom.
(2) A zinc halogenide complex and a tautomer of the same which are represented by the formula (2): 
where each of R11, R12, R13, R14, R15, R16, R17, R18, R19, R20, R21, R22, R23, R24, R25, R26, R27, R28, R29 and R30 is individually a hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino , substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, and each of X1 and X2 is individually a fluorine, chlorine, bromine or iodine atom.
(3) A zinc complex and tautomer of the same which are represented by the formula (3): 
where each of R31, R32, R33, R34, R35, R36, R37, R38, R39, R40, R41, R42, R43, R44, R45, R46, R47, R48, R49 and R50 is individually hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group.
(4) A quinoline compound which has peak intensity at a Bragg angle (2 xcex8) of 12.8xc2x0, 15.2xc2x0, 18.3xc2x0, 22.5xc2x0, 25xc2x0 and 28.4xc2x0 on a X-ray diffraction spectrum and is shown by the formula (7): 
(5) A quinoline compound of the formula (7) wherein the peak intensity ratio of the Bragg angle (2xcex8) of 12.8xc2x0 to the Bragg angle (2xcex8) of 15.2xc2x0 is 0.7 or less.
(6) A preparation process of a quinoline compound and a tautomer of the same which are represented by the formula (4): 
where each of R51, R52, R53, R54 R55, R56, R57, R58, R59, R60, is individually hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, comprising reacting a quinoline derivative represented by the formula (5) 
where each of Y1, Y2, Y3, Y4, Y5 and Y6 is a hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, and a phthalimide derivative represented by the formula (6): 
where each of Y7, Y8, Y9 and Y10 is individually a hydrogen atom, halogen atom, nitro, cyano, hydroxy, amino, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, substituted or unsubstituted N-alkylamino, substituted or unsubstituted N,N-dialkylamino, substituted or unsubstituted N-arylamino, substituted or unsubstituted N,N-diarylamino or substituted or unsubstituted N-alkyl-N-arylamino group, with zinc halogenide in an organic basic solvent and successively treating with an inorganic acid.
(7) A preparation process of a quinoline compound and a tautomer which are represented by the formula (4) wherein a phthalimide derivative represented by the formula (6) is in a molar ratio of 0.5 to 2.0 to a quinoline derivative represented by the formula (5).
(8) A preparation process of a quinoline compound and a tautomer which are represented by the formula (4) wherein a phthalimide derivative represented by the formula (6) is in a molar ratio of 1.1 to 2.0 to a quinoline derivative represented by the formula (5),
(9) A preparation process of a quinoline compound represented by the formula (4) and a tautomer of the same comprising treating with an inorganic acid a zinc halogenide complex represented by the formula (2) and a tautomer of the same.
(10) A preparation process of a quinoline compound represented by the formula (4) and a tautomer of the same comprising treating with an inorganic acid a zinc complex represented by the formula (3) and a tautomer of the same.
(11) An electro-luminescence element wherein the luminous layer is a compound represented by the formula (4) and a tautomer of the same.
(12) A fluorescent material comprising a quinoline compound represented by the formula (4) and a tautomer of the same.
(13) A preparation process of a zinc halogenide complex represented by the formula (2) and a tautomer of the same comprising reacting one or two kinds of a quinoline derivative represented by the formula (5) and one or two kinds of a phthalimide derivative represented by the formula (6) with zinc halogenide in an organic solvent.
(14) A preparation process of a zinc halogenide complex represented by the formula (2) and a tautomer of the same comprising reacting a quinoline compound represented by the formula (4) and a tautomer of the same with zinc halogenide in an organic solvent.
(15) An electro-luminescence element wherein the luminous layer is a zinc halogenide complex represented by the formula (2) and a tautomer of the same.
(16) An ultraviolet absorption material comprising a zinc halogenide complex represented by the formula (2) and a tautomer of the same.
(17) A preparation process of a zinc complex represented by the formula (3) and a tautomer of the same comprising heating in organic amine a zinc halogenide complex represented by the formula (2) and a tautomer of the same.
(18) A preparation process of a zinc complex represented by the formula (3) and a tautomer of the same comprising reacting one or two kinds of a quinoline derivative represented by the formula (5) and one or two kinds of a phthalimide derivative represented by the formula (6) with zinc halogenide in an organic solvent.
(19) An electro-luminescence element wherein the luminous layer is a zinc complex represented by the formula (3) and a tautomer of the same.
(20) An ultraviolet absorption material comprising a zinc complex represented by the formula (3) and a tautomer of the same.
The present invention provides the compound represented by the formulas (2), (3) and (4) and a tautomer of the same as an EL material which has a strong luminescent intensity, the compound represented by the formulas (2) and (3) and a tautomer of the same as a specific ultraviolet absorption material which has absorption at a wave length of 400 nm or less, and further the compound represented by the formula (4) and a tautomer of the same as an excellent fluorescent material which has a strong luminescent intensity.
Further, the present invention can prepare these useful materials by related preparation processes directly from the quinoline derivative represented by the formula (5) and the phthalimide derivative represented by the formula (6), or by way of the quinoline compound represented by the formula (4) which is obtained from these derivatives.
That is, the invention provides excellent materials for the EL material, ultraviolet absorption material and fluorescent material, and a useful process of preparing these materials.